Overwhelm, Despair, Self-Doubt & Other Fun Adventures on the Road to Success

take risks, dream big

As a former ad agency employee and current copywriter for hire, it’s no surprise that Mad Men was one of my favorite shows. (Although in my ad agency days, unfortunately – or fortunately, depending on how you look at it – it wasn’t customary to have a fully stocked bar in the office, or cocktails in the middle of the day.)

So when the season finale aired a few weeks ago, I watched with great joy as my favorite characters’ stories got wrapped up neatly, along with a twinge of overwrought mourning that the whole shebang was coming to an end.

The day after the final episode (and who am I kidding, for days to come), I found myself reading more, more and still more about Mad Men, and especially its creator, Matthew Weiner.

And I happened upon this article in which Weiner discusses his rocky and challenge-filled road to success with honesty and transparency.

In the piece, excerpted from a book called Getting There: A Book of Mentors and published on Fast Company, Weiner talks about how artists “frequently hide the steps that lead to their masterpieces.” This can lead to discouragement for those of us trying to create something meaningful, he says, because all we see is the finished product, and compare our work to that.

He goes on to say “I always swore to myself that I would not hide my brushstrokes.”

Shortly after reading that piece, I read Melissa Cassera’s blog post, “Don’t hide your brushstrokes,” where she talks about Weiner’s article and the application of its ideas to business.

I love what Melissa says here:

“By glossing over all of the ‘unsexy’ points of your journey — all the brushstrokes — you’re doing a disservice to your fans, clients, customers, everyone in your business audience, and quite honestly, everyone you meet.

By pretending that it’s all ‘easy’ and ‘perfect’ and ‘drama free,’ you’re missing an opportunity to actually HELP somebody.”

At the end of the post she asks:

“What’s the toughest, unsexiest moment you can remember from your business / career history? Share your ‘brushstroke moment’ and what you learned. Feel free to do it in the comments below. Or, better yet, share it with your own community.”

And that inspired me to write about one of my own “brushstroke” moments here.

I previously shared this story with my email subscribers, but it felt too personal to talk about on the blog. But what the heck? Melissa’s post changed my mind.

(By the by, this is one of many, many “brushstroke moments” I’ve had in the last 2-3 years of taking my copywriting business from a side hustle to my full-time source of income. And I’m still having them.  Weekly. There’s enough to fill a book I tell ya, but today we’ll start with just the one. :))

Here’s the story I recently shared with my email subscribers:

So, did I ever tell you that right around this same time last year, I was so exhausted, stressed and overwhelmed that I almost considered giving up on the idea that it was possible to have a satisfying, happiness-inducing, lucrative business doing work I love, for clients I love?

No?

Well, let me give you a little bit of the skinny here.

In May of 2014 I was working a long-term corporate freelance writing gig for a big organization, one that offered a lot of nice perks, but also imposed many stress-inducing deadlines, and required me to work on site in an environment that made me wildly unhappy (my breath gets shallow just thinking about it).

I was also running my copywriting and web marketing consulting business at the time, which I adored but . . . by necessity it remained a “side business” to be squeezed in and around my corporate writing gig obligations.

So here I was, making a pretty decent living as a copywriter, with plenty of projects on tap for the corporate client (a situation those of us who sell our writing services actually dream of), but I was working 7 days a week to keep up with both that work and my side hustle, and frankly, not enjoying my life very much.

It was a despairing cocktail of non-stop obligations, deadlines, and 12 hour days, most of which were spent doing work I didn’t love. And with that schedule, I didn’t have enough time left over in a week to optimize my business, my website, or my offerings – which meant until something changed, I’d always be stuck with my overwhelming workload, at my current revenue plateau.

Since my most cherished value is “freedom,” working this way made me feel like a tiger pacing a cage – imprisoned, and none too happy about it. I was desperate to change things, but how?

One of my most vivid memories of this time is sitting in Panera Bread one night with one of my closest friends, sobbing into my caesar salad about my work life and my obligations, barely able to breathe. (Between the crying and the gasping for breath, my friend actually offered to take me to urgent care. True story.)

Obviously, I could not go on this way.

The trouble was, I had I no idea HOW, exactly, I could change my situation. I was in no position to just up and leave the corporate writing gig, but there was no way on earth I wanted to give up on my dream of creating the copywriting business of my dreams either.

Especially since achieving that dream would allow me the space and time freedom to work on a book that’s been gnawing at me for over a year – and I had yet to get started on.

But one of the great things that happened for me during that time – the thing I credit with eventually helping me get beyond it all – was reading publicity and business strategist Selena Soo’s emails in which she shared her story about once being in a very similar situation.

She was working in PR, yet not making much money, even though she was working non-stop. And she was uncomfortable with some of the pressure involved in get results for PR clients. And because she never established clear boundaries in her work, she was working early mornings, nights and weekends.

Almost every detail of what she described felt like what I was going through. And she had actually turned her situation around, to great success – she quit that iteration of her PR business, changed her business model, and started offering coaching and consulting services, which got her to $157,000 in revenue in the first year of her new business.

And best of all, she did it on a schedule that didn’t consume every waking moment of her life, which sounded like pure bliss to me. Because making a nice income is great, but only if it comes with time freedom and a flexible schedule as well – that’s the ultimate prize, in my book.

I was intrigued by Selena’s story, and honestly, envious.

So when she announced her Get Known, Get Clients (GKGC) program last May, I hopped on board almost immediately. [The program is now closed, but if you’re curious, you can read the review I wrote about GKGC and the results I got from it right over here.]

It was through working with Selena last year and applying the advanced strategies she teaches that I was finally able to leave my corporate writing gig in February of this year and go fully out on my own with my copywriting and web marketing consulting business.

Now I’m much happier, more fulfilled, and I actually have free time. Not a lot mind you, but way more than I did this time last year.

And I’m gung-ho and ready to rumble with my business again. I can’t believe that this time last year I actually thought of throwing in the towel, even for a second.

There are still challenges, of course. And lots more work to be done. So much so that some days, if I’m honest, I long for the ease of just having to show up at a regular gig again.

Luckily, that sentiment quickly passes.

If I could offer any encouragement to anyone going through something similar, anyone on the verge of chucking the dream of supporting themselves with their creative business for the so-called security of employment, I’d say think long and hard before you make that deal with the devil. There’s probably some way you can turn things around, as I did (and as Selena did).

Just remember, you’re trading your life energy – time you’ll never get back – for what you do to earn a living, so make sure you’re happy with the choice.

 

[Want to learn to write copy that connects with your ideal clients? Sign up for free weekly updates and get instant access to the CREATIVE REBEL GUIDE TO WRITING A CLIENT-ATTRACTING ABOUT PAGE, plus copywriting & web marketing tips and other fun stuff for creative freelancers & biz owners that I only share with my subscribers, delivered straight to your inbox each Tuesday.]

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